Methanamine, hydrochloride (1:1) → 1-[5-(4-Fluorophenyl)-2-methyl-1-(phenylsulfonyl)-1H-pyrrol-3-yl]-N-methylmethanamine hydrochloride

HRID 554413Notes

Reaction equation

HRID 554413 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:15])=[O:14])[C:11]([CH3:22])=[C:10]([CH:23]=O)[CH:9]=2)=[CH:4][CH:3]=1.[Cl-:25].C[NH3+].[C:28]([BH3-])#[N:29].[Na+]>CO>[ClH:25].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:15])=[O:14])[C:11]([CH3:22])=[C:10]([CH2:23][NH:29][CH3:28])[CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11637Methanamine, hydrochloride (1:1)HCID 5003444Sodium cyanoborohydrideHCID 866207465-(4-Fluorophenyl)-2-methyl-1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde

Product 1

HCID 669252011-[5-(4-Fluorophenyl)-2-methyl-1-(phenylsulfonyl)-1H-pyrrol-3-yl]-N-methylmethanamine hydrochlorideYield 65.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution (20 mL) of 5-(4-fluorophenyl)-2-methyl-1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde (0.40 g) in methanol were added methylammonium chloride (0.95 g) and sodium cyanoborohydride (0.30 g), and the mixture was stirred at room temperature for 20 hr. The reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogencarbonate solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=1:0→1:2) to give free base of the title compound as an oil (0.30 g). The obtained oil (0.30 g) was dissolved in ethyl acetate (6 mL), and a 4 mol/L hydrogen chloride-ethyl acetate solution (3 mL) was added. The mixture was concentrated under reduced pressure, and the residue was crystallized from ethyl acetate to give the title compound as colorless crystals (yield 0.31 g, 92%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogencarbonate solution
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=1:0→1:2)

Sources & evidence

ORD record
ord-53a7de76c02042e397eb7645d1242ffe
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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